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  • 1
    Electronic Resource
    Electronic Resource
    Convenient synthesis of diethyl 3-methylisoxazoline and isoxazolephosphonates, potent synthons to biological active compounds (1992)
    New York, NY : Wiley-Blackwell
    Journal für Praktische Chemie/Chemiker-Zeitung 334 (1992), S. 278-280 
    Details
    ISSN: 0941-1216
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/prac.19923340314
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  • 2
    Electronic Resource
    Electronic Resource
    Improved Synthesis of Anhydrohexitol Building Blocks for Oligonucleotide SynthesisDedicated to Professor Wolfgang Pfleiderer on the occasion of his 70th birthday. (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1453-1461 
    Details
    ISSN: 0947-3440
    Keywords: Antisense agents ; Nucleosides ; Nucleobases ; Carbohydrates ; Alkylation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of the four building blocks used for the preparation of hexitol nucleic acids were optimized. The nucleoside analogues with a purine base moiety are best prepared by a nucleophilic substitution reaction, whereas the pyrimidine nucleosides can best be obtained using Mitsunobu-type conditions.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970724
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  • 3
    Electronic Resource
    Electronic Resource
    Species differences in the chirality of the carbonyl reduction of [14C] fenofibrate in laboratory animals and humans (1989)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 1 (1989), S. 197-201 
    Details
    ISSN: 0899-0042
    Keywords: fenofibrate ; chiral reduction ; species differences ; prochiral to chiral transformation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The prochiral carbonyl group of fenofibrate (isopropyl 2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl propionate) is reduced during its metabolism giving rise to a chiral secondary alcohol, “reduced fenofibric acid.” Chiral and diastereomeric HPLC methods have been developed for the determination of its enantiomeric composition and these have been applied to the measurement of the “reduced fenofibric acid” enantiomers in urine of rats, guinea pigs, dogs, and human volunteers given [14C]fenofibrate. In the three animal species, the reduction is markedly enantioselective for the (-)-isomer, the enantiomeric ratios (-/ +) being 95:5. This was not due to differences in the excretion of the enantiomers, since when racemic “reduced fenofibric acid” was given to rats it was recovered in the urine with the same enantiomeric composition as the dose form. In humans the ratio was 52:48 showing the lack of stereoselectivity of reduction in this species.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530010304
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  • 4
    Electronic Resource
    Electronic Resource
    Preparative resolution of some 5,5-hydantoin derivatives via formation of diastereoisomeric saltsThis paper was presented at the Second International Symposium on Chiral Discrimination, May 27-31, 1991, Rome, Italy. (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 4 (1992), S. 400-403 
    Details
    ISSN: 0899-0042
    Keywords: solvent ; basic medium ; competitive solubilities ; optimization ; optical resolution ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Several preparative resolutions of 5,5-disubstituted hydantoins have been achieved via fractional crystallization of diastereoisomeric salts. The process can be extended by making use of the difference between the variation of solubilities of the hydantoins and their salts with α-methylbenzylamine as a function of the alkalinity of the medium. Optimization for each resolution procedure involves a refinement of the excess amount of base needed. © 1992 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530040612
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  • 5
    Electronic Resource
    Electronic Resource
    Glutathione conjugation and pharmacokinetics of 2-bromo-3-phenylpropionic acid in vitro and in the rat in vivo (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 4 (1992), S. 407-414 
    Details
    ISSN: 0899-0042
    Keywords: GSH conjugate ; pharmacokinetics ; biliary excretion ; chiral ; 2-bromo-3-phenyl propionic acid ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Glutathione (GSH) conjugation of the chiral compound 2-bromo-3-phenylpropionic acid (BPP) was studied in vitro and in the rat in vivo. GSH conjugation of BPP, catalyzed by a mixture of glutathione-S-transferases (GST's) from rat liver cytosol in vitro, was stereoselective: at a substrate concentration of 250 μM, (R)-BPP was more rapidly conjugated than (S)-BPP (R/S-ratio = 2.6). The blood elimination kinetics of the separate BPP enantiomers and the biliary excretion kinetics of the corresponding GSH conjugates were studied in the rat in vivo after administration of (R)- or (S)-BPP at a dose level of 50 μmol/kg. Elimination of (R)-BPP from blood was faster than that of (S)-BPP: half lives were 9 ± 2 min for (R)-BPP and 13 ± 1 min for (S)-BPP. The biliary excretion rate of the GSH conjugate of (R)-BPP declined monoexponentially, while that of the GSH conjugate of (S)-BPP displayed a biphasic profile. Half lives of excretion were 13 ± 1 for the GSH conjugate of (R)-BPP, and 11 ± 2 for the GSH conjugate of (S)-BPP (second phase). The first phase in the biliary excretion of the GSH conjugate of (S)-BPP could not be attributed to capacity limitation of biliary transport carriers as higher excretion rates were attained upon administration of higher doses (100 and 200 μmol/kg) of ((S)-BPP). The blood elimination profiles of (R)- and (S)-BPP differed greatly from the biliary excretion profiles of the corresponding GSH conjugates. This suggests that the kinetics of BPP conjugate excretion are determined by other processes than hepatic GSH conjugation. © 1992 Wiley-Liss, Inc.
    Additional Material: 8 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530040702
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  • 6
    Electronic Resource
    Electronic Resource
    Enantioselectivity in the induction of peroxisome proliferation by 2-ethylhexanoic acid (1992)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 4 (1992), S. 478-483 
    Details
    ISSN: 0899-0042
    Keywords: enantiomers ; nonchiral chromatography ; palmitoyl coenzyme A oxidation ; plasticizer ; rat hepatocytes primary culture ; racemate ; resolution ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The stereoselectivity of the peroxisome proliferation potency of 2-ethylhexanoic acid (2-EHA), a metabolite of the plasticizer di-(2-ethylhexyl) adipate, was investigated in vitro. The enantiomers of 2-EHA were prepared via the semipreparative HPLC resolution of their diastereoisomeric (+)-(R)-1-phenylethylamine derivatives and the subsequent hydrolytic cleavage. Monolayers of hepatocytes were incubated 3 days with solutions of ( - )-(R), (+)-(S), and (±)-2-EHA. The peroxisome proliferation potency was measured by means of determination of the peroxisomal palmitoyl coenzyme A oxidation. The theoretical induction component due to each enantiomer were calculated from the experimental data considering the enantiomeric purities of the acids. The (+)-(S)-enantiomer was found to be the most potent inducer, e.g., the eutomer, while the ( - )-(R) was the distomer. The eudismic ratio was about 1.6 and the racemic mixture exhibited an intermediary potency. These results, obtained in vitro in conditions avoiding confounding factors such as pharmacokinetics, suggest that the peroxisome proliferation induced by 2-ethylhexanoic acid is a stereoselective phenomenon. © 1992 Wiley-Liss, Inc.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530040804
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  • 7
    Electronic Resource
    Electronic Resource
    Current regulatory (draft) guidance on chiral medicinal products: Canada, EEC, Japan, United States (1994)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 6 (1994), S. 72-75 
    Details
    ISSN: 0899-0042
    Keywords: chirality ; racemate ; enantiomers ; regulation ; review ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The rapid development of stereospecific analytical, synthetic, and preparative methods has profoundly changed the prospects for development and application of chiral medicinal products. This has induced regulatory agencies, e.g., in Canada, the EEC, Japan, and the United States, to prepare guidance on this subject. The present draft documents are discussed, with emphasis on the two most important cases: (1) New racemates: How many extra requirements are justified? (2) Development of a single enantiomer from an approved racemate: how few are acceptable? At the moment the opportunities for early harmonisation are favourable and the formulation of one international guidance document seems feasible. © 1994 Wiley-Liss, Inc.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chir.530060206
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  • 8
    Electronic Resource
    Electronic Resource
    Considerations about the chirality of the saturated six-membered rings with two or more heteroatoms (1996)
    New York, NY [u.a.] : Wiley-Blackwell
    Chirality 8 (1996), S. 311-315 
    Details
    ISSN: 0899-0042
    Keywords: virtual triligand chiral center ; chirality of saturated heterocycles with six-membered ring ; rules for the specification of the configuration ; desymmetrization of adamantane ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The chirality of the title heterocycles is discussed considering their genesis by desymmetrization of the corresponding adamantanes. Some rules for the specification of the absolute configurations of the enantiomers (R or S) for this type of compounds are proposed. © 1996 Wiley-Liss, Inc.
    Additional Material: 10 Ill.
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  • 9
    Electronic Resource
    Electronic Resource
    The Influence of the Axial Chirality of Dibenzo[a,c]cyclooctene on the Configuration of Its Photo-Diels-Alder Adducts (1994)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 77 (1994), S. 850-858 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Triazole-diones and naphthoquinone are shown to add in a photochemical [4+2] reaction to the strongly twisted title diene 1. With 1, 4-naphthoquione, the process is also accompanied by a [2+2] cycloaddition. When the pure atropisomer (-)-1 is irradiated in presence of 2, 3-dichloro- 1, 4-naphthoquinone (9), the axial chirality of the diene is preserved. Moreover, it is found to exert complete control over the chirality induced in the resulting spiro-dihydropyrane 10. Absolute configuration are determined by X-ray crystallography. In absence of a photo-dienophile, the axially chiral, dextrorotatory 6-phenyldibenzo[a,ccyclootene] ((++)-11) undergoes a stereospecific electrocyclization to give levorotatory 4b,6a-dihydro-5-phenylcyclobuta[l]phenanthrene ((-)-13). Thus, only one out of two possible, disrotatory modes of ring closure is preferred.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19940770324
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  • 10
    Electronic Resource
    Electronic Resource
    Synthesis, Structure, and Antimalarial Activity of Some Enantiomerically Pure, cis-fused cyclopenteno-1,2,4-trioxanes (1995)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 78 (1995), S. 647-662 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two pairs of enantiomerically pure cis-fused cyclopenteno-1,2,4-trioxanes (7, ent-7 and 8, ent-8) are prepared (Schemes 1-3). Their identities are established by dye-sensitized photo-oxygenation of ent-7 and 8, ent-8 to the allylichydroperxides, reduction to the corresponding alcohols, and conversion to the (1S)-camphanates (Scheme 4), the structures of which are determined by X-ray analysis. The dynamic properties of ent-7 are investigated by NMR spectroscopy and PM3 calculations. Evidence for an easily accessible twist-boat conformation is obtained. The in vitro and in vivo antimalarial activities of 7, ent-7,8, and ent-8 as well as those of the racemic mixtures are evaluated against Plasmodium falciparum, P. berghei, and P. yoelii. No correlation is observed between configuration and activity. Racemates and pure enantiomers have commensurate activities. The mode of action on the intraerythrocytic parasite is rationalized in terms of close docking by the twist-boat conformer of the trioxane on the surface of a molecule of heme, single-electron transfer to the O—O σ* orbital, and scission to the acetal radical which then irreversibly isomerizes to a C-centered radical, the ultimate lethal agent (Scheme 5).
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19950780312
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